26 Jan Snag the Best Advisors for Your Startup, From Best-Selling Authors to Fortune 500 CEOs
by Brooke Hauser Aug 23, 2018
Amy Chang is just one of those people. You know the kind. You meet them in passing at an event and immediately feel like you’ve known them for years. They surprise you with kindness and generosity upfront. They seem to have some secret that lets them to talk to anyone with an openness and humor that makes them magnetic.
So it won’t surprise you that Chang, who ran product for Google Analytics before founding data-driven networking startup Accompany in 2013, counts dozens of luminaries among her advisors — including best selling authors like Chip Heath and Nir Eyal. Fielding this type of expertise seems like a nearly impossible feat, but her only secret is this: She spent years figuring out how to methodically build her network — and is the first to admit she feels the same nervousness, intimidation and doubt that any first-time founder feels when asking seasoned professionals for help.
Through both wins and losses in this arena, she forged new emotional intelligence and muscles that have enabled her to surround herself with the best thinking across marketing, data, engineering, and more. Here, she shares hard-won lessons from her vast experience for founders and individuals alike who are looking for a different caliber of advice.
Advising is not one size fits all. Different people will be capable of different time and energy commitments. So, the first thing you should do is create categories of advisors that allow for this variability. For instance at Accompany, Chang has what she calls “light touch advisors” and “board advisors” (they’re not on the board, it’s just meant to signify deep involvement).
Light touch advisors have no regular obligations. Chang simply wants to reserve the right to call them and have a 30-minute conversation a few times a year when an issue in their wheelhouse pops up. Board advisors, on the other hand, are intimately familiar with all aspects of the company, get regular updates, and are on-call to help sort through critical decisions.
Having these two buckets has given Chang a lot more latitude to get incredibly talented yet busy people involved. She can assess what’s appropriate, and can ask for their time accordingly. She’s also able to set clear and reasonable expectations from the beginning. While she has under 5 board advisors, this model gives her access to the minds of 30+ other incredible operators for one-off questions.
This system also lets her label everyone involved as an advisor regardless of whether they’re advising on just one area or on ten. Giving the title of ‘advisor’ communicates just how much Chang values their time and advice, which in turn strengthens the connection.
Light Touch Advisors
You want a circle of area experts who you can call to quickly get help solving specific problems, says Chang. “Keep the lift low for them,” she says. “When you ask them to advise, tell them that this will mean pinging them a few times a year, and it will only and always be about something they know more about than nearly anyone else on earth.”
Light touch advisors help on an ad hoc basis. For example, when Accompany’s staff wants a second pair of eyes or a gut check on a new feature, they might pull in Slack VP Product April Underwood. Dan Ariely was able to offer a better welcome flow for the app, drawing on several behavioral truths he’s been researching for years. “These are people who’ve seen the movie enough times to know how it will end. It’s very easy for them to tell us what will happen when we take specific actions, what we should watch out for, how to do things better,” she says.
“All you’re asking for here is 20 minutes,” Chang says. “If someone was jazzed enough about you to say yes to being any kind of advisor, they’ll say yes to 20 minutes. And most of the time you’ll learn more than you could have in a year because that person knows so much more than you and is able to pattern match based on a wealth of experience.”
Being a founder is perpetually needing more expertise than you could ever possibly accrue as an individual. This is the way to get close.
In addition to bestowing the “advisor” title, Chang strongly recommends granting these people a small, courtesy amount of equity. It’s a professional way to say thank you while acknowledging their vested interest in your success.
If you start noticing that some of these light-touch contacts becoming indispensable, especially at pivotal moments, don’t wait for them to bring it up. Ask them if they want to take on a larger advising role, and match it with a larger stake in the company.
Board Advisors (a.k.a. Senior Advisors, Lead Advisors — the title is up to you.)
Lorrie Norrington is Chang’s first call whenever she’s wrestling with a big decision. She’s one of Accompany’s three board advisors, and exemplifies who you want in this type of position.
“Board advisors have enough context about the entire team and the status of the company to weigh in meaningfully on any decision. But at the same time, they’re the people you should be able to most open up to and be vulnerable with,” she says.
Chang met Norrington incidentally at Stanford’s Director Consortium. They struck up a conversation after a session and talked all the way through the break. Now she relies on her for completely unvarnished opinions on the thorniest questions she encounters.
“The reason it works so well is that I know with 100% certainty that nothing I tell her will change the way she thinks about me — even if I don’t follow her advice,” says Chang.
This level of psychological safety is non-optional for a successful close advising relationship, she says. It stems from trusting that even the toughest, most unflinching criticism isn’t personal — it’s about helping the company succeed. When choosing advisors, look for people whose style of delivery never makes you feel judged.
“When we raised our series B, when we decided to build our own data platform — there have been many inflection points where the answers were not even close to black or white,” Chang says. “Each of those times, I pinged three of our most insightful and incisive board advisors. They pushed and refined my thinking.”
Deciding to build Accompany’s own proprietary data platform was a high stakes undertaking. It was going to be expensive, hard, long, slogging work that would demand even more funding, and Chang wasn’t sure it was the right call. That is, until Norrington and fellow board advisors Kevin Compton and Dave Goldberg told her, unequivocally, how vital it would be long term.
“It was really scary,” she says. “I had to be able to lean on them pretty hard.” So when you’re looking for your ‘board advisors,’ keep this anecdote in mind. Who do you want in your corner, knowing they’ll see you during some of the most draining, defeating, terrifying moments of your career? If you don’t want someone to see you that way, they aren’t right for the job.
Maximize Potential Connections
“You have to be willing to meet hundreds of people every single year of your career,” says Chang. “Maybe you’ll have chemistry with 10% where you want to spend more time with them and they want to spend more time with you.” Building your network is not an extracurricular. It takes hard, intentional work. She still carves out time to meet with at least two new people a week.
“When I started out, I would ask the people I knew who their best and brightest contacts were for X — where X was maybe sales or software engineering. Then I’d ask for intros,” she says. “I met and met and met and met people. If I felt chemistry, I followed up. If we ran out of things to talk about after talking one or two times, I didn’t pursue. If there was more density, I took note.”
90% of starting a company is execution, and that definitely applies to advising relationships, she says. You have to do the work to cultivate relationships, which means allocating time to support others toward their goals. Make it clear you’ll be there (not just in spirit, but immediately and concretely) if there’s ever anything you can help with.
If you’re just starting out today, don’t worry. You know people. Start asking them who they know and build outward in concentric circles, says Chang. “Whenever someone says to you, ‘You should really talk to person X about Y,’ don’t let it go by. Write it down. Follow up and make it happen. Lots of people forget about intros they’ve been offered and will never know what could have happened. You can meet someone who will change your life anywhere.”
Finding the right advisors comes down to chemistry, and that can only be tested face-to-face.
Be ambitious, and don’t sell yourself short by assuming someone won’t talk to you. Chang, for instance, likes to reach out to the authors of business books she likes. That’s how she met Heath. She read Made to Stick, found a common connection, and asked for an intro. Of course she didn’t ask him to advise right away, she simply asked for 10 minutes of his time to chat about his work. Since then, he’s helped Accompany rethink its brand messaging.
“Authors have fantastic domain expertise and they love talking to people who have been affected by their writing,” she says. “So, think creatively about the pieces you already have in place. Who are the top three people who pop into your brain when you think ‘growth’ or ‘sales’ or ‘SEO’? Find mutual connections if you can. Now ask your existing contacts the same questions. Who do they think of? Would they feel comfortable making an intro?”
Events are great for networking, but they can also be a waste of time. Despite her social savvy, Chang still gets nervous when she finds herself at a reception where she knows no one. When this happens, she gives herself a pass instead of stressing out about making conversation. Instead, she advises carefully choosing events where you’ll have a way in.
“Make sure you’re familiar with at least 10% of the folks who will likely be there,” she says. “That’ll give you the foothold to productively meet a lot of other people. Your existing contacts can help break the ice and establish your credibility.”
Redefine the Word “Chemistry”
“Lorrie has kicked my ass so many times. She pushes me to the edge of the yellow-zone and I love her for it,” says Chang. “Soon after launch, when the last thing we were thinking about was expanding to yet another platform, Lorrie was the person who said, ‘This information has to be in my inbox, you need an app for Gmail.’” So the team jammed on the idea and were able to get a product out the door within two weeks.
Feeling chemistry with a prospective advisor doesn’t mean feeling total synchronicity or agreement. It’s not the same as feeling like someone “really gets you” or “finally understands.” Instead, you want someone who lights you up intellectually, says things that make you want to ask questions, and isn’t afraid to make controversial statements about what you or your company are doing. Chemistry is when someone is more interested in ensuring the best for your company than tiptoeing around your ego.
How can you spot this in a first conversation?
- Maybe they ask you questions about the future that feel a bit uncomfortable.
- Maybe they introduce other possibilities or markets or challenges in the conversation.
- Maybe they ask how you plan to accomplish key milestones.
- Maybe they display curiosity in how you plan to do what you’re saying and run an unsolicited stress test of your ideas and arguments.
“In a close advisor, you want someone who will ask you the really gut-wrenching questions before your board inevitably asks them,” says Chang. “I know I can be completely vulnerable with Lorrie in a way I can’t be with almost anyone else because she’s operating with a different purpose.”
Norrington’s tough questioning is the best preparation for board meetings, but it’s not soft or forgiving. Too many entrepreneurs ring themselves with advisors who feed their confirmation bias, or who won’t risk upsetting them, even if that’s exactly the push they need.
Here’s a good indication of a great advisor: Every time you walk away or hang up the phone, you feel like you need to spend more time with them.
This is why it’s so important to test the depth of someone’s knowledge over a couple meetings before you ask them to officially advise you. There should be more than enough material to fill a few coffee dates. And their wisdom should ideally manifest in forcing you to do most of the thinking and talking.
Turning an initial meeting into an advising relationship is where the bulk of EQ is needed. Of course, don’t just plunge in and ask immediately. There’s no way to even know if you’re a match. But something must come before asking for that initial coffee too.
If you’ve had a great conversation at an event, or you’ve been introduced to someone by a mutual contact, send a follow-up email to ask for a short phone call. Very few people will turn down a 20-minute conversation, especially if you’re specific about what you want to discuss. They won’t want to “just chat” — they’ll want to know what value you’re looking to get from them, so don’t be shy about it.
One call is enough to see if there’s enough mutual interest and content to keep talking. If yes, ask for lunch or coffee in the next two weeks to keep things going. If it goes well but you’re not sure the person is fully bought into what you’re working on, don’t abandon the connection.
“I’ll wait for a relevant article to pop up about the person on Accompany, or about something that might interest them, and I’ll send it along with a congrats or ask how they’re doing,” says Chang. “If I spot an opportunity to be helpful, like an intro to a potential board member or backchanneling a candidate they’re interested in, I’ll volunteer.” She sees every communication as a chance to show why she and Accompany are worth their time.
Make it clear you're about mutual benefit. You're not just asking for their help. You're dedicated to helping them as well.
Put your best foot forward. Only make double opt-in introductions, and read over your emails before sending. Polish and etiquette matter more than you think. If someone seems increasingly interested or grateful for your assistance, that’s when to ask for an in-person meeting.
Here’s what you should be looking for in meetings and correspondence:
- Is the person responsive to you? Even if they’re not wildly enthusiastic about your ideas, do they get back to you relatively quickly?
- Do they ask questions to get more context about what you’re doing? Are they curious to understand the big picture?
- Do they seem judgmental in an unproductive way? In casual conversation, do they gossip or unconstructively criticize other people or companies? If so, they’ll make you feel judged too.
- Are they proactive about finding ways to help you? Do they suggest other people you should meet or ideas to consider without you asking?
- Would this person be more helpful at a different stage of your company? If so, keep them in mind. Do they know anyone else they’d recommend you speak to?
- Does the person’s network overlap a lot with yours? Too much? Can they open enough doors to people and fields you have no contact with already?
Making the Ask
Asking someone to advise your company is like asking someone on a first date. Nerves, butterflies — even some light panic — is totally normal. Here’s how Chang’s navigated it successfully in the past:
- Start with a question. Ease into the topic by asking if the person currently advises companies. If so, do they do more informal, lighter touch advising? See if they respond positively. They’ll know where you’re leading, but you won’t have to put yourself out there right away. If they say no, you can let it go — no harm, no foul.
- When you do ask, be clear. Don’t try to find other words or talk around what you want. Say straight out: I think you’d be an incredible advisor for our company.
- Quickly talk scope of commitment. Before you pause or let them talk, set clear expectations around time investment. If you’re asking for a lower-lift engagement, say specifically that it will be 20 minutes every other month on an ad hoc basis. “I tell people, ‘You have world-class knowledge in this domain, I would love to be able to consult you when relevant things come up,’” says Chang. “People are much more likely to say yes if they feel like you get it — you get that they’re busy, you have the EQ to know what’s reasonable to ask for.”
- Be patient. Wait for their answer. Don’t talk over them or interrupt. You might feel the urge to counter any objection or argument. Don’t. React slowly and give yourself enough time to think.
- Respond with enthusiasm. If you get a yes, immediately show gratitude and explain how thrilled you will be to build alongside them. If it’s a no, show empathy for their reasoning. They’ll remember how you behaved in that moment.
Remember, you’re asking for their most valuable resource. Don’t propose it if you don’t feel like the person really wants to see you and your company win. If you don’t know for sure that they do, it’s too early to be asking at all. You have more work to do relaying your passion for the idea.
I never knew how important storytelling was until I became an entrepreneur. Success in these conversations is all about the energy of the connection. Smile. Be excited! It matters.
Keeping Relationships Strong
Advisory relationships tend to be so qualitative, it’s hard to define metrics for success. The best indications of a healthy connection for Chang are: 1) whether or not an advisor is responsive to the company’s needs on a regular basis, and 2) whether you feel like you ‘quantum-leap’ your knowledge on a topic whenever you speak to the person.
As an entrepreneur, there are several actions you can take to boost these metrics:
- Know what it means to follow up. This is the most important thing you can do. Whatever advice someone gives you, tell them how it was considered, acted on or applied, and what happened as a result. “The thing people like Lorrie and Chip care most about is whether their time yielded impact,” says Chang. She keeps a running document of one-liner ideas contributed by advisors and makes a point of revisiting every six months so she can follow up.
- Send regular updates. It’s critical to stay top of mind. Chang sends short email updates to all of Accompany’s advisors periodically, talking through new features and providing commentary on recent decisions. “Usually I get replies from ~40% of them every time,” she says. “It’s a great way to solidify contact. And they often supply a ton of good input unsolicited.”
- Circulate low-lift tasks. You can keep people feeling engaged by sending out very quick tasks to help the company. For example, when Accompany was about to launch notifications, they wanted to know if the feature felt helpful or spammy. They sent a quick note to advisors asking them to test it out and share their thoughts. “We ended up making our notifications much more specific as a result,” Chang says.
- Make asks that match the person. Everyone has regular preferences and behaviors. Some people like to tweet a lot. Others would rather speak at events. Know what type of request would fit with what they love or feel natural doing. “We think about how our advisors choose to express themselves, their style of writing, what types of things they usually share, the channels they share on,” says Chang. “It’s worth it to be nuanced. Document it. Before a launch, I’ll sit with our marketing team and run through our advisors, pointing out who makes sense to ask for what kind of support, and who wouldn’t feel comfortable.”
- Bring them into the team. Don’t keep the relationship unilateral. Invite an advisor in to speak informally with your team — it’s a nice way to introduce them to everyone. Host a dinner for them with the team around a big question the company is wrestling with. It will cut out the small talk. If an advisor seems suited to it, ask them to mentor one of your star players. It will make them feel helpful and benefit someone you might not have time to train and develop yourself.
- Don’t hold back. You’re only hurting yourself if you’re not 100% vulnerable and transparent with your closest advisors. This includes being honest about your emotions. Seasoned professionals make the best advisors because — like therapists — they’ve seen everything. They’ve seen people get upset, angry, sad, scared, and they’re equipped to deal with it. “Give your close advisors a chance to help you with not just the issue, but your psychology around the issue too,” says Chang. “It’s an incredible relief.”
- Express constant and continual gratitude. This is critical. “Your advisors are in no way obligated to help you. They want to know their time is being well spent,” she says. Letting them know specifically where and how they had impact on the product, the team, on you is essential.
As with any skill you learn as an entrepreneur, you need to practice to build the right muscles. EQ is too often considered an innate quality that you either have or don’t. That’s not the case. The biggest mistake people make when it comes to finding advisors is not being proactive enough — they don’t meet enough people, or follow up fast enough, or take enough meetings to make sure it’s truly a match. If you put in the time, you’ll develop the pattern matching and the instincts will follow.And don’t worry about being nervous. Everyone is. Even the people you’re asking for help get nervous sometimes. That same humanity allows you to project authentic passion that will make the right people want to work with you.